Microwave-Assisted Synthesis of Modified Glycidyl Methacrylate–Ethyl Methacrylate Oligomers, Their Physico-Chemical and Biological Characteristics

In this study, well-known oligomers containing ethyl methacrylate (EMA) and glycidyl methacrylate (GMA) components for the synthesis of the oligomeric network [P(EMA)-co-(GMA)] were used. In order to change the hydrophobic character of the [P(EMA)-co-(GMA)] to a more hydrophilic one, the oligomeric chain was functionalized with ethanolamine, xylitol (Xyl), and L-ornithine. The oligomeric materials were characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopy, scanning electron microscopy, and differential thermogravimetric analysis. In the final stage, thanks to the large amount of -OH groups, it was possible to obtain a three-dimensional hydrogel (HG) network. The HGs were used as a matrix for the immobilization of methylene blue, which was chosen as a model compound of active substances, the release of which from the matrix was examined using spectrophotometric detection. The cytotoxic test was performed using fluid extracts of the HGs and human skin fibroblasts. The cell culture experiment showed that only [P(EMA)-co-(GMA)] and [P(EMA)-co-(GMA)]-Xyl have the potential to be used in biomedical applications. The studies revealed that the obtained HGs were porous and non-cytotoxic, which gives them the opportunity to possess great potential for use as an oligomeric network for drug reservoirs in in vitro application.

Tailoring Poly(lactic acid) (PLA) Properties: Effect of the Impact Modifiers EE-g-GMA and POE-g-GMA

Poly(ethylene-octene) grafted with glycidyl methacrylate (POE-g-GMA) and ethylene elastomeric grafted with glycidyl methacrylate (EE-g-GMA) were used as impact modifiers, aiming for tailoring poly(lactic acid) (PLA) properties. POE-g-GMA and EE-g-GMA was used in a proportion of 5; 7.5 and 10%, considering a good balance of properties for PLA. The PLA/POE-g-GMA and PLA/EE-g-GMA blends were processed in a twin-screw extruder and injection molded. The FTIR spectra indicated interactions between the PLA and the modifiers. The 10% addition of EE-g-GMA and POE-g-GMA promoted significant increases in impact strength, with gains of 108% and 140%, respectively. These acted as heterogeneous nucleating agents in the PLA matrix, generating a higher crystallinity degree for the blends. This impacted to keep the thermal deflection temperature (HDT) and Shore D hardness at the same level as PLA. By thermogravimetry (TG), the blends showed increased thermal stability, suggesting a stabilizing effect of the modifiers POE-g-GMA and EE-g-GMA on the PLA matrix. Scanning electron microscopy (SEM) showed dispersed POE-g-GMA and EE-g-GMA particles, as well as the presence of ligand reinforcing the systems interaction. The PLA properties can be tailored and improved by adding small concentrations of POE-g-GMA and EE-g-GMA. In light of this, new environmentally friendly and semi-biodegradable materials can be manufactured for application in the packaging industry.

Preparation of Antimicrobial Coatings from Cross-Linked Copolymers Containing Quaternary Dodecyl-Ammonium Compounds

One of the concerns today’s societies face is the development of resistant pathogenic microorganisms. The need to tackle this problem has driven the development of innovative antimicrobial materials capable of killing or inhibiting the growth of microorganisms. The present study investigates the dependence of the antimicrobial activity and solubility properties on the hydrophilicity/hydrophobicity ratio of antimicrobial coatings based on quaternary ammonium compounds. In this line, suitable hydrophilic and hydrophobic structural units were selected for synthesizing the antimicrobial copolymers poly(4-vinylbenzyl dimethyldodecylammonium chloride-co-acrylic acid), P(VBCDDA-co-AA20) and poly(dodecyltrimethylammonium 4-styrene sulfonate-co-glycidyl methacrylate), P(SSAmC12-co-GMA20), bearing an alkyl chain of 12 carbons either through covalent bonding or through electrostatic interaction. The cross-linking reaction of the carboxylic group of acrylic acid (AA) with the epoxide group of glycidyl methacrylate (GMA) of these two series of reactive antimicrobial copolymers was explored in blends, obtained through solution casting after curing at various temperatures. The release of the final products in pure water and NaCl 1 M solutions (as analyzed by gravimetry and total organic carbon, TOC/total nitrogen, TN analyses), could be controlled by the coating composition. The cross-linked polymeric membranes of composition 60/40 w/w % ratios led to 97.8 and 99.7% mortality for Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus), respectively, whereas the coating 20/80 w/w % resulted in 96.6 and 99.8% cell reduction. Despite the decrease in hydrophobicity (from a 16- to a 12-carbon alkyl chain), the new materials maintained the killing efficacy, while at the same time resulting in increased release to the aqueous solution.